Triethylamine → 5-bromo-N-(3,5-difluorophenyl)nicotinamide

HRID 240525

반응식

HRID 240525 반응식
C(Cl)(=O)C(Cl)=O.[Br:7][C:8]1[CH:9]=[N:10][CH:11]=[C:12]([CH:16]=1)[C:13]([OH:15])=O.[F:17][C:18]1[CH:19]=[C:20]([CH:22]=[C:23]([F:25])[CH:24]=1)[NH2:21].C(N(CC)CC)C>C(Cl)Cl.C(O)(=O)C.CN(C=O)C>[Br:7][C:8]1[CH:9]=[N:10][CH:11]=[C:12]([CH:16]=1)[C:13]([NH:21][C:20]1[CH:19]=[C:18]([F:17])[CH:24]=[C:23]([F:25])[CH:22]=1)=[O:15]

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 887075-Bromonicotinic acidHCID 965953,5-Difluoroaniline

생성물 1

HCID 416011495-bromo-N-(3,5-difluorophenyl)nicotinamide수율 93%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

Oxalyl chloride (1.2 mL) and DMF (25 μL) were added to 5-bromonicotinic acid (1.0 g, 4.95 mmol) suspended in CH2Cl2 (30 mL). The resulting mixture was stirred at room temperature for 12 min. It was then concentrated to dryness and azeotroped with toluene. The residual was then dissolved in toluene (30 mL). 3,5-Difluoroaniline (1.0 g, 7.8 mmol) was added followed by triethylamine (1.1 mL, 7.5 mmol). The resulting suspension was stirred at room temperature for 10 min. The reaction mixture was taken in 5% acetic acid(aq) (300 mL) and extracted with ethyl acetate (2×200 mL). The combined organic extract was washed with 1.0 M Na2CO3(aq) (2×100 mL) and brine. The organic layers were combined, dried (Na2SO4) and concentrated to dryness to provide the title compound (1.4 g, 93%). MS (APCI) m/z 313, 315 (M+H)+.

후처리

  1. concentrationIt was then concentrated to dryness
  2. customazeotroped with toluene
  3. dissolutionThe residual was then dissolved in toluene (30 mL)
  4. stirringThe resulting suspension was stirred at room temperature for 10 min
  5. extractionextracted with ethyl acetate (2×200 mL)
  6. extractionThe combined organic extract
  7. washwas washed with 1.0 M Na2CO3(aq) (2×100 mL) and brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-43a336d3036a41efac28a8d6ccaa9a9b
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08648084B2

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